Water → HCID 178428028, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the product of Example 26B (194 mg, 0.27 mmol) in concentrated sulfuric acid (5 mL) was added water (1 mL) at 0° C. and the mixture was stirred at 95° C. for 20 minutes. After cooling to ambient temperature, water (3 mL) was added. The mixture was adjusted to pH 8-9 with saturated sodium bicarbonate solution and extracted with dichloromethane (3×20 mL). The organic layers were concentrated under vacuum and the residue was purified via preparative HPLC using a gradient of 10/90 to 75/25 acetonitrile/water (containing 0.1% trifluoroacetic acid) to give the title compound. 1H NMR (DMSO-d6, 300 MHz): δ 13.62 (br, 1 H), 11.4 (br, 1 H), 9.58 (br, 1 H), 8.66 (s, 2 H), 8.58 (s, 1 H), 7.75-7.57 (m, 3 H), 7.45 (d, J=9 Hz, 1 H), 6.78 (d, J=2.4 Hz, 1 H), 6.34 (dd, J=9, 2.4 Hz, 1 H), 4.70 (s, 2 H), 3.26-3.22 (m, 8 H), 2.23 (s, 3 H). MS: 510 (M+H+).

Provenance & Evidence